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Paper | Regular issue | Vol 100, No. 12, 2020, pp.2050-2060
Published online, 23rd September, 2020
DOI: 10.3987/COM-20-14340
Stereoselective Synthesis of (Z)-3-Arylidene-2-oxindoles via a Palladium-Catalyzed Tandem Reaction

Sunhwa Park, Kye Jung Shin, and Jae Hong Seo*

*College of Pharmacy, The Catholic University of Korea, 43 Jinong-ro Wonmi-gu Bucheon, Gyeonggi-do, 14662, Korea


A novel and efficient synthetic method for the stereoselective preparation of (Z)-3-arylideneoxindoles from simple propiolamide has been developed utilizing a palladium-catalyzed tandem reaction. Two Sonogashira and reductive Heck reactions were successfully combined under microwave irradiation. The E/Z stereoselectivity of the reaction was enhanced by solvent control.